While the squash is baking, brown your ground beef in a large skillet over medium heat, then drain and remove the browned beef from the skillet.
Saute apple, garlic, and onion in the same pan over medium heat for another 5-7 minutes, or until softened, stirring occasionally.
Stir beef back into the skillet, then turn off the heat and mix in the cinnamon, nutmeg, cumin, cayenne, sea salt, and dried cranberries.
Turn the cooked squash over so that the cut side is up, then fill each with the ground beef & apple mixture. Top each filled squash with a bit of shredded cheddar, then return them to the oven and bake for another 15-20 minutes at 375 degrees, or until cheese is browned and squash is very tender.
Enjoy your cooked acorn squash with their sweet + savory filling!
Next time I'd chop the apples smaller than shown here, so that they blend in a little bit better.